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AXIT CACBOXILIC I.

nh ngha, phn loi, danh php a) nh ngha: Axt cacboxilc l loi hp cht hu c c cha nhm cacboxyl (-COOH) lin kt vi gc hircacbon trong phn t. Cng thc tng qut l R(COOH)x. b) Phn loi: Ty theo bn cht ca gc hircacbon ngi ta phn chia axt thnh cc loi: axt cacboxilc no nh CH3COOH, C2H5COOH, axit cacboxilic khng no nh CH2=CH-COOH, HOOC-CH=CH-COOH v axt thm nh C6H5COOH. Ty theo s lng nhm cacboxyl trong phn t axt m ngi ta phn chia axt thnh cc loi axt monocacboxilc, axt icacboxilc,... c. Danh php: * Cch gi thng thng: nhiu axt cacboxilc mang tn gi theo ngha lch s, tc l theo tn ca ngun nguyn liu hoc ngun gc t nhin tm ra axt . Nh axt fomic HCOOH c tch ra t con kin c tn formica theo ting latinh. Nhiu axt c coi l dn xut ca axt axetc CH3COOH nh CH3CH2COOH (axt metyl axetc), C6H5CH2COOH (axt phenyl axetc). * Danh php IUPAC Tn ca axt cacboxilc = axt + tn hircacbon + oc Th d: HCOOH axt metanoc CH3CH2COOH axt propanoc Nu mch cacbon phc tp hn th chn mch cha nhm -COOH lm mch chnh, khi nh s mch chnh bt u t nhm -COOH. Th d: TN THNG THNG CA MT S AXT THNG GP ii/- Ho tnh: a. Bn cht v c im nhm cacboxyl (-COOH): Cng thc cu to ca axt mncacboxylc c th biu din nh sau: Trong nhm cacboxyl l nhm chc quyt nh tnh cht ho hc ca axt. N l s t

hp ca nhm cacbonyl v nhm hiroxyl (-OH). xut hin hiu ng lin hp gia cp electron t do ca oxi trong nhm OH vi cc electron p trong lin kt i ca nhm cacbonyl C = O. Kt qu l lin kt trong axt phn cc mnh hn hn so vi lin kt O-H trong ancol, iu gii thch tnh axt ca axt cacboxilc mnh hn ancol. ng thi lin kt C=O trong nhm cacboxyl km phn cc hn lin kt C=O trong aneht v xeton, do nhm C=O trong axt khng cn c cc phn ng ging nhm C=O trong aneht v xeton. Ngoi ra nhm cacboxyl l nhm ht in t lm cho Ha linh ng d b thay th v n l nhm nh hng loi II i vi nhn thm. b) Tnh axt: * Khi tan trong nc axt phn li rt yu theo phng trnh Nu gc R cha cc nhm y in t (+I, +C) lm cho lin kt ()trong nhm (COOH) km phn cc hn lm cho axt yu i. Nu gc R cha cc nhm ht in t (-I, -C) s lm tng phn cc ca lin kt ) trong nhm (COOH), do lm tng tnh axt. Th d: Tnh axt ca mt s axt cacboxilc gim theo trt t sau: FCH2COOH > ClCH2COOH > BrCH2COOH > HCOOH > > CH3COOH > CH3CH2COOH > CH2CH2COOH * Axt cacboxilc c y mi tnh cht ca axt: tc dng vi mt s kim loi mnh, tc dng vi baz v oxt baz, tc dng vi mui ca axt yu hn. Th d:

Cc gc axt

c gi theo tn ca axt tng ng i ui c thnh ui t. c l axetat natri, c l benzoat natri. Cc mui ny khi tan trong nc b thy phn mnh cho mi trng kim. c) Cc phn ng thay th nhm OH to dn xut ca axt: * Phn ng to halogenua axt. Cc hp cht mang helogen nh PX5 , PX3, SOCl2 s thay th nhm OH ca nhm cacboxyl bng halogen (X). Th d: * Phn ng este ha: + S chung: + C ch: Tt c cc giai on u thun nghch nn phn ng este ha l thun nghch. Th d: d) Phn ng cacboxyl ha (loi nhm cacboxyl): nhit cao c xc tc cc axt b mt CO2 thnh ankan: e) Phn ng th gc hyrocacbon: * Khi chiu sng th Cl2 c th thay th ln lt 1, 2 hoc c 3 nguyn t cua CH3COOH. Phn ng ny xy ra theo c ch gc ging nh khi halogen ha ankan * Trong axt benzoc nhm COOH lm phn ng hot ha nhn thm i vi tc nhn electronphin (phn ng kh khn hn so vi benzen ). Phn ng th xy ra ch yu v tr meta. f) Phn ng kh: Cc cht kh thng nh: H2(Ni); Zn/HCl; Na/C2H5OH khng kh c axt. Nhng c th kh axt thnh ru bng LiAlh5 iii) iu ch axt cacboxilic a) Oxi ha cc hp cht hu c: Cc hp cht hu c nh ankan, anken, aren, ru, anht, xetn khi xi ha bng xi khng kh c xc tc s to thnh axt nh: b) Thy phn cc dn xut ca axt cacboxilc.: S chung: dn xut axt RCOY vi Y l -Hal, RO-, -NH2 Th d: c) Cng vo hp cht c magi: Th d:

2. Dn xut ca axt cacboxilc i) nh ngha, phn loi: Khi thay th nhm OH nhm cacboxyl bng nhng nhm th khc nhau ta c dn xut ca axt cacboxilc. Cng thc tng qut c dng: Trong R l gc hircacbon, Halogenua axt l gc axyl, Y l cc nhm th nh: (Y l halogen)

ii) Danh

Anhirt Este Amt

axt (Y (Y Danh

(Y l l

RCOO-) RO-) -NH2) php:

php

ca

halogenua

axt

Xut pht t tn ca axt cacboxilc tng ng thay axt... c thnh ... yl halogenua. Th d: axetyl clorua

Danh php ca anhirt axt xut pht t tn ca axt tng ng nhng thay axt bng anhirt. Th d: (CH3CO)2O anhirt axetc. Danh php ca este l tn gc axt v tn gc ankyl ca ru . Th d: CH3COOC2H5 este axetat atyl. Danh php ca amt l tn ca axt tng ng b ch axt v i ui c thnh amt. Th d: CH3CONH2 axetamt. iii) Tnh cht ha hc: a) Th RCOOR + H2O D RCOOH + Phn ng thy phn: d: ROH

- C ch phn ng thy phn dn xut ca axt tng t c ch phn ng este ha: + C ch phn ng thy phn este xc tc axt SN2.

Tt c cc giai on trong c ch u l thun nghch nn H+ va xc tc cho phn ng este ha li va xc tc cho phn ng thy phn. + C ch phn ng thy phn este xc tc baz. SN2

Trong c ch ny c giai on cui cng l bt thun nghch, nn ton b phn ng l bt thun nghch, do khng th thc hin phn ng este ha trong mi trng kim. b) Tc dng vi hp cht c kim theo s :

c) Khi 3. i) b Este Halogenua Amt axt kh

Phn bi b b b LiAlh5 kh kh

ng hoc thnh thnh kh ru thnh Na/C2H5OH 2 qua

kh: th: ru: aneht amin Lipt chung:

Khi

nim

Lipt l tn chung ca cht bo (du m ng thc vt) v cc cht ging cht bo gi l Lipt (sp, sterot, photphatt) - Cht bo l este ca glyxerin v cc axt bo cao, c cng thc chung: Cc gc R1, R2, R3 c th ging hoc khc nhau, chng thng l cc gc ankyl ca cc axt: C15H31COOH (axt panmitc),C17H35COOH (axt Stearc), C17H33COOH (axt lec). - Sp c thnh phn ch yu l este ca axt monocacboxilc no hay khng no vi ancol n chc c khi lng phn t ln. Trong axt v ancol thng c s cacbon chn t 16 n 36 nh este mirixyl panmitat: C15H31COOC31H63 ii) Tnh cht: * Cc cht bo khng chng ct c, v ngay p sut thp cht bo b phn hy trc khi bay hi.

* Cht bo c gc axt khng no thng th lng (du thc vt, du c...) c nhit nng chy thp hn so vi cht bo c gc axt no thng th rn (m ng vt). * Cht bo d tan trong cc dung mi hu c nh este, benzen, xng,..., khng tan trong nc. * Cht bo d b thy phn bi kim to thnh glyxerin v cc mui ca axt hu c (x phng) cn gi l phn ng x phng ha. Th * C th chuyn du lng thnh m rn nh phn ng hir ha c xc tc Ni. * Du m lu ngoi khng kh s b i, c mi kh chu do chng b thy phn hoc b xi ha to thnh axt, aneht, xeton c mch ngn c mi kh chu. V vy trong cng nghip thc phm ngi ta bo qun du m bng cch thm vo chng cc cht chng xi ha. * ngoi khng kh mt s du thc vt nh du lanh cng c th ha rn do qu trnh trng hp v oxi ha phc tp. * Cc o cht bo c mt s ch s c trng. d:

Ch s axt: l s mg KOH dng trung ha axt bo t do c trong 1gam cht bo. o Ch s x phng ha biu th bng s mg KOH dng x phng ha hon ton 1gam cht bo. o Ch iii) s it X l s gam I2 v c th cht cng hp ty vo 100gam ra cht tng bo. hp:

phng

a) X phng: X phng l mui natri hoc kali ca cc axt bo cao, ch yu l axt Starc v axt panmitc C17H35COONa(K) C15H31COONa(K). Trong k ngh ngi ta sn xut x phng bng cch thy phn cht bo bng kim.

X phng natri l khi rn, cn x phng kali thng mm hoc lng. Trong nc x phng b thy phn mnh theo phng trnh. Khi gp nc cng (nc cha nhiu ion Ca2+ v Mg2+) th axt va thy phn s b kt ta lm gim kh nng ty ra ca x phng. phn t x phng c dng ko di vi mt nhm a nc mt u (COO- ) v mt gc hircacbon di k nc mt u (R). Nu trn x phng vi cht hu c th u k nc ca x phng gc (R) s quay v pha cht hu c bao bc ly cht hu c, cn u a nc s hng ra ngoi. N lm gim sc cng b mt ca cht hu c. Trong nc cc nhm a nc s li ko cht hu c khuch tn vo dung dch x phng v tri theo nc. b) Cht ty ra tng hp:

V cu to cht ty ra tng hp cng ging nh x phng chng u c nhm k nc v nhm a nc, nhng nhm a nc ca cht ty ra tng hp l gc ca axt sunfurc. Cng thc chung l R-SO3Na. Th d nh C12H25C6h5SO3Na oxibenzen sunfunat natri

Tc dng ty ra ca cht ty ra tng hp cng ging nh x phng, chng u lm gim sc cng b mt, tng kh nng thm t v l cht nh tng ha, lm cho cht bn d khuych tn vo nc. Nhng khc vi x phng, cht ty ra tng hp khng b kt ta bi nc cng, do n c dng c trong mi trng nc cng v mi trng axt. Read more: http://hoahoc.org/showthread.php?t=4712&page=1#ixzz0veg91tFw